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When I’m home, he’s in a diaper and free to roam around. When I’m not, I keep him in the crate. I walk him 2x a day, he’s a yorkie that’s 14. I adopted him around a month ago and was told that he is well behaved and potty trained. Well behaved? Well he’s quiet and stays to himself but he doesn’t listen and has a lot of accidents. I was close to giving him away but want to consider potty training him again.
 

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How long is "all day?" Sometimes dogs that age (just like older humans) need more frequent potty breaks.
 

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When you are working could you confine him to just one room like a kitchen or laundry room? Or maybe set up a pen indoors to give him a little more room? 8-9 hours is way too long to be in a crate.
 

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It is fine. I would be sure to get him out as son as you get home and be sure to get him out frequently to avoid accidents.
Dogs do not generalize behavior well. He was likely house broken at his last home but did not generalize the behavior to the new home. So, treat him like a puppy and retrain it. the reality is that at 14 he is not going to live a lot longer.. 2-3 years is my guess at the outside but that does not mean he cannot learn things.
 

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8-9 hours (a normal work day) is not usually too long for a healthy adult dog. At that age, however, sometimes the bladder is not as strong as it was.

Have you had him vet checked for an underlying medical issue? There are medications for incontinence.
 
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